Ammonia → 5-(Benzyloxy)-2-(hydroxymethyl)-1,4-dihydropyridin-4-one

HRID 1249595Notes

Reaction equation

HRID 1249595 reaction equation
[OH:1][CH2:2][C:3]1O[CH:5]=[C:6]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:7](=[O:9])[CH:8]=1.[NH3:18].[OH-].[NH4+]>C(O)C>[OH:1][CH2:2][C:3]1[NH:18][CH:5]=[C:6]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:7](=[O:9])[CH:8]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 14923Ammonium HydroxideHCID 9015985-(benzyloxy)-2-(hydroxymethyl)-4H-pyran-4-one

Product 1

HCID 28015645-(Benzyloxy)-2-(hydroxymethyl)-1,4-dihydropyridin-4-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-(hydroxymethyl)-5-[(phenylmethyl)oxy]-4H-pyran-4-one (9.65 g, 41.59 mmole), 95 ml of concentrated ammonia and 20 ml of ethanol were heated at reflux overnight. An additional 75 ml of ammonium hydroxide was added, the mixture was refluxed for 2 hours and cooled. The resulting brown solid was filtered and washed with water until the washings were neutral. The crude product was suspended in ethanol, filtered, washed with ethanol and hexane and dried in vacuo. The yield of the title compound was 7.61 g.

Workup

  1. temperaturewere heated
  2. temperatureat reflux overnight
  3. temperaturethe mixture was refluxed for 2 hours
  4. temperaturecooled
  5. filtrationThe resulting brown solid was filtered
  6. washwashed with water until the washings
  7. filtrationfiltered
  8. washwashed with ethanol and hexane
  9. customdried in vacuo

Sources & evidence

ORD record
ord-6f219c6f9da04028b3b57e31293aec97
Source dataset
uspto-grants-1986_12
Patent number
US04632985

Reaction notes

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